New total synthesis of the marine antitumor alkaloid (-)-agelastatin A |
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Authors: | Domostoj Mathias M Irving Ed Scheinmann Feodor Hale Karl J |
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Institution: | The Christopher Ingold Laboratories, The Chemistry Department, University College London, 20 Gordon Street, London WC1H 0AJ, United Kingdom. |
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Abstract: | reaction: see text] A new total synthesis of (-)-agelastatin A (1) has been achieved from the chiral oxazolidinone (-)-3. Although enone transposition was problematic when the Michael ring closure of 2 was attempted with strong base, the desired cyclization could be effected with Hunig's base after the pyrrole nucleus was brominated. Subsequent reduction and monobromination afforded synthetic (-)-agelastatin A (1). |
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